Marilyn Monroe kicked off the trend in 1953 as the first-ever Playboy cover star, and dozens of icons since have adorned the cover of the magazine, now a byword for unapologetic sexiness. If you. From Marilyn Monroe to Kristy Garett, Playboy: The Complete Centerfolds, 1953-2016 is chock-full of nude photos (734 centerfolds to be exact) alongside an essay by bestselling author.